Vacation rentals in Oakland

Spring is in the air at our Lake View Condo!

Gorgeous Lake View!! Centrally located 3 story condo on Deep Creek Lake. Enjoy all 4 seasons on the lake. Ski Wisp is 5 mins away. Walking distance to shops and restaurants. 2 bedrooms and 2 full baths. 3rd floor is the loft with bunk beds. Brand new kitchen with new cabinets, granite and stainless appliances. Cathedral ceilings throughout. Wood burning fireplace. Large deck with a beautiful lake view. Come relax and play on the lake or the mountain. Enjoy everything Deep Creek has to offer!

Bird's Eye View

Nestled high amidst the sturdy branches, "Bird's Eye View" is a sanctuary suspended between earth and sky. Located less than 5 minutes from Deep Creek Lake and perched among the foliage, our treehouse offers a panoramic perspective of the surrounding forest, granting its visitors an unparalleled vantage point to observe nature's wonders. Relax in the hot tub and take in an amazing sunset. The home is a harmonious blend of locally-crafted art and furniture to add rustic charm and modern comfort.

The Original Hob

We have the Original Hob and Molly (separate listing) overlooking our creek at the point of 7 little waterfalls for your sleeping and hangout pleasure! A shared sweet kitchen and bath completes the 3 small structures. Full bath plus an outdoor shower makes for great accommodations. We're within 5 miles of State Parks and Deep Creek Lake. Come see the Garrett County stars, hear the creek and birds and be a million miles from where you are. Friendly dogs are welcomed -see "other things to note".

Mountain Air Oasis with Hot Tub

Relax with the whole family or friends at this peaceful private 2 acre property, close to Maryland's natural attractions! A family-friendly three bedroom home 1,380 sq. ft secluded in a rural neighborhood. Wildlife to watch and enjoy! Relax with a campfire or soak in the hot tub! We are located approximately 30 minutes from Swallow Falls State Park, Deep Creek Lake, and Black Water Falls State Park. We are also within 10 minutes of two wedding venues (The White Barn, and Twin Tales Event Farm).

Honeymoon Spa Experience! Pond! Sauna! Hot Tub!

High End, Romantic Escape with Private Pond nestled in the pines, located 1 mile from Deep Creek Lake State Park, Custom Sauna, Hot Tub, Outdoor TV, Cozy Rocking Chairs, Propane Fire Pit, Soaking Tub, Robes, Plush King Bed, Espresso Machine, Margaretaville Margarita Machine, Firepit by the pond, Sound Appealing? Then this is the place for you! Re-connect with your signifiant other in a spa like, mountain setting. We provide all the essentials and much more! Just 15 minutes from Wisp Resort.

Dancing Bears

***PLEASE NO PETS*** Meticulously maintained authentic log cabin in the woods getaway! Our 800 sf cabin has two bedrooms, one bathroom and large bonus 3rd bedroom/loft area (queen bed, two cots, kids' play area, TV and home office space). Our location is secluded yet conveniently located to all of the activities Deep Creek Lake has to offer. The property backs up to 65 wooded acres at the end of a private road. Peaceful setting with a stream, fire pit, picnic table, and horse shoe pit.

SUGARBUSH - Sweet Serenity Tiny House

Welcome to SUGARBUSH! "Suga" is a 450 sq. ft. custom built tiny house. She will comfortably accommodate 2 adults or a family with 2 small children. AGE REQUIREMENT to book this space is 25+. At this time we DO NOT allow pets. Suga sits on a 3+ acre lot that use to be used for cross country skiing. She got her name from two trails, Sugarbush Run and Sugarbush Shortcut that ran through the lot! We welcome you to stay and enjoy our wonderful little getaway here in Pleasant Valley.

Captain's Quarters Deep Creek Log Cabin Oasis

Welcome to our slice of peace and relaxation in beautiful Deep Creek! Spacious and serene log cabin. The Captains Quarters is the perfect getaway. 2BDRM, propane fireplace (Nov-Apr), full kitchen, and a 6+ person hot tub. Dogs welcome but please let us know and pay the fee. 2 comfy Queen mattresses, towels and linens provided, hi speed internet, smart TV’s, and Bluetooth soundbar. Relax in our two heated massage chairs in the family room. We want to earn a 5 star review!

Victorian Farmhouse with view of pleasant valley

A tall farmhouse with high ceilings and a big backyard on a gentle wooded hillside. We have 4 bedrooms with a queen bed in each and 1 bedroom with 2 twin beds, also a crib in the master bedroom. A great space for cookouts with a view of Backbone mountain and the farm land of Pleasant Valley. You'll be 25 minutes from the Wisp resort at Deep Creek Lake and less than 5 minutes outside of the town of Oakland with the historic B&O railroad museum.

Stone Haven

Welcome to Stone Haven — a cheerful stone cottage just minutes from Deep Creek Lake. Guests love Stone Haven for its charm, cleanliness, thoughtful touches, cozy atmosphere, and convenient location near the lake, Wisp Resort, hiking trails, restaurants, and local shops. Whether you’re visiting for lake days, skiing, hiking, or a quiet weekend away, Stone Haven offers a relaxing and comfortable place to return to after exploring the area.

Peaceful nature retreat nestled in a forested area

Welcome to our lovely vacation House! Built in 2024, fresh, cozy and modern. Perfect for memorable family trip, romantic getaway for a couple or a fun adventure for a small group of friends. Convenient location- great combination of privacy (forest-like area) and quick access to fun places: 5-10 minutes drive from Wisp Ski Resort, Deep Creek lake, boat rentals, scenic hikes, restaurants, bars, amusement parks and grocery stores.

Lakehound Lodge - lake view, pet friendly

Cozy cabin in the middle of all that Deep Creek Lake area has to offer! Enjoy a dip in the hot tub by the fire with peekaboo lake views under twinkle lights. This three level cabin boasts a bedroom and bathroom on each level, two wood burning fireplaces, two living rooms, and an enclosed side porch with hot tub. Pets welcome for a fee. Close to the lake, Wisp, parks, golfing, fishing, and much more! Follow insta @lakehoundlodge